(1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl 4-nitrobenzoate | 866454-14-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl 4-nitrobenzoate
• CAS: 866454-14-0
• 化学式: C₂₆H₂₅N₃O₄
• 分子量: 443.502
• InChiKey: UKHBEBHEGHJJFR-LQTXRJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.57
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl 4-nitrobenzoate 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 (1S,3R,4S,8S,9R)-9-azido-cinchonane
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008
• 作为产物：
  描述：

  对硝基苯甲酸 、 辛可尼丁 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl 4-nitrobenzoate
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008

文献信息

• Synthesis of novel 9<i>R/S</i>-acyloxy derivatives of cinchonidine and cinchonine as insecticidal agents
  作者：Zhi-Ping Che、Jin-Ming Yang、Song Zhang、Di Sun、Yue-E Tian、Sheng-Ming Liu、Xiao-Min Lin、Jia Jiang、Gen-Qiang Chen

  DOI：10.1080/10286020.2020.1729136

  日期：2021.2.1

  discover biorational natural products-based insecticides, two series (27) of novel 9R/S-acyloxy derivatives of cinchonidine and cinchonine were prepared and assessed for their insecticidal activity against Mythimna separata in vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially derivatives 6l and 6o exhibited the best insecticidal activity with final mortality rates of 75

  摘要 努力发现基于生物理性天然产物的杀虫剂，制备了两类（27）新的辛可尼定和辛可宁的9 R / S-酰氧基衍生物，并通过叶浸法以1 mg的剂量评估了它们对体内Mythimna separata的杀虫活性。/毫升 在所有化合物中，尤其是衍生物6l和6o表现出最好的杀虫活性，最终死亡率分别为75.0％和71.4％。总的来说，游离的9-羟基不是杀虫活性的先决条件，并且C9取代具有良好的耐受性。C8 / 9位的构型对于杀虫活性是重要的，而9 S构型是最佳的。6'-OCH 3 部分不是必需的，也可以将其除去。